3563-49-3

Basic information

• Product Name: Pyrovalerone
• Synonyms: 1-(4-Methylphenyl)-2-(pyrrolidin-1-yl)-1-pentanone;4'-Methyl-α-(pyrrolidin-1-yl)valerophenone;1-(4-methylphenyl)-2-pyrrolidin-1-ylpentan-1-one
• CAS NO: 3563-49-3
• Molecular Formula: C₁₆H₂₃NO
• Molecular Weight: 245.364
• EINECS: 214-556-9
• Mol File: 3563-49-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: bp0.08 104°
• Flash Point: 127.3°C
• Appearance: /
• Density: 1.019g/cm³
• Vapor Pressure: 1.93E-05mmHg at 25°C
• Refractive Index: 1.535
• CAS DataBase Reference: Pyrovalerone(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrovalerone(3563-49-3)
• EPA Substance Registry System: Pyrovalerone(3563-49-3)

Safety Data

• Hazardous Substances Data: 3563-49-3(Hazardous Substances Data)

Usage

Uses

Stimulant (central).

InChI:InChI=1/C16H23NO/c1-3-6-15(17-11-4-5-12-17)16(18)14-9-7-13(2)8-10-14/h7-10,15H,3-6,11-12H2,1-2H3

Upstream product

• 123-75-1 pyrrolidine 
• 850352-48-6 2-bromo-1-(4-methylphenyl)pentan-1-one 
• 1671-77-8 n-butyl p-tolyl ketone 
• 638-29-9 n-valeryl chloride 
• 108-88-3 toluene 
• 1147-62-2 O-2371 
• 110-62-3 pentanal 
• 91763-35-8 1-(p-methylphenyl)-1-pentanol 
• 106-38-7 para-bromotoluene 
• 7642-17-3 1-Methyl-4-((E)-pent-1-enyl)-benzene 

Downstream Products

• 850352-03-3 1-phenyl-3-pyrrolidin-1-yl-2-(p-tolyl)-hexan-2-ol hydrochloride 
• 850352-36-2 (R)-2-pyrrolidin-1-yl-1-(p-tolyl)-pentan-1-one dibenzoyl-D-tartrate 

Relevant articles and documents

1,3-Dibromo-5,5-dimethylhydantoin (DBH) mediated one-pot syntheses of α-bromo/amino ketones from alkenes in water

α-Bromo ketones are versatile intermediates of high practical utility. Traditional approaches to these compounds are restricted to a relatively hazardous/complex reagent combination, a long reaction time, the use of non-environmentally friendly solvents, or a limited substrate scope. Herein, we describe the development of a new methodology for the preparation of α-bromo ketones from alkenes using 1,3-dibromo-5,5-dimethylhydantoin (DBH) as a bromine source and an oxidant simultaneously. This easy to carry out two-step one-pot protocol proceeds in water and provides high yield of a great variety of α-bromo ketones. Addition of an amine to the intermediate α-bromo ketone further enables the preparation of α-amino ketones in a one-pot sequence.

1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors

Dopamine, serotonin, and norepinephrine are essential for neurotransmission in the mammalian system. These three neurotransmitters have been the focus of considerable research because the modulation of their production and their interaction at monoamine receptors has profound effects upon a multitude of pharmacological outcomes. Our interest has focused on neurotransmitter reuptake mechanisms in a search for medications for cocaine abuse. Herein we describe the synthesis and biological evaluation of an array of 2-aminopentanophenones. This array has yielded selective inhibitors of the dopamine and norepinephrine transporters with little effect upon serotonin trafficking. A subset of compounds had no significant affinity at 5HT1A, 5HT1B, 5HT1C, D1, D2, or D3 receptors. The lead compound, racemic 1-(4-methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one 4a, was resolved into its enantiomers and the S isomer was found to be the most biologically active enantiomer. Among the most potent of these DAT/NET selective compounds are the 1-(3,4-dichlorophenyl)- (4u) and the 1-naphthyl- (4t) 2-pyrrolidin-1-yl-pentan-1-one analogues.